Rufus Wainwright Goes Wild in Watermill; The Transom Thumbs a Ride

“It gets a little nutty,” sighed the singer Rufus Wainwright at the 15th Annual Watermill Summer Benefit in Southampton on Saturday, July 26. “When they bring the horse in… there will be a horse. Being auctioned off. So that’ll be fun.”

The evening’s dress code was “decadent chic.” Mr. Wainwright wore a green leopard print suit (“It’s Viktor & Rolf. And they made it specifically for me”) over a shirtless, kind-of-hairy chest, accessorized with an avant-garde mass of jewels by Justin Giunta. “I actually wore it once for my Judy Garland concert in London,” he said, of the suit. “And for ‘decadent chic,’ I thought, There’s nobody more decadent or chic than Judy! So I took it out of the closet.” Indeed!

The vast lawn area behind artist and producer Robert Wilson’s modernist Watermill Center resembled a surrealist cocktail party (Mr. Wainwright’s boyfriend, Jorn Weisbrodt, is the center’s creative director). Among the guests were professional cougar Kim Cattrall, toting much-younger boyfriend Alan Wyse (a Smith Jerrod doppelgänger); Howard Stern and fiancée Beth Ostrovsky, poured into a gold Herve Leger dress; and socialites Amanda Hearst, Cristina Greeven Cuomo and Fabiola Beracasa. There was also a man in red high heels and a spandex body suit with several massive balls protruding from his head. A tiki-torched pathway led to a wooded area in which bandaged, asylum-looking youth twitched against trees with giant white boxes on their heads. Solemn drummers sat in formation on the grass; guests sipped pink drinks involving tequila. (This was nothing compared to last year, muttered one guest, when an overweight, naked woman covered in red paint had poured milk on her head).

“This is always the best party of the summer,” said novelist and wine aficionado Jay McInerney, who was wearing a white suit. “It’s something other than going and drinking crappy wine and eating rubber chicken for charity, you know? This is really fun.”

He was standing next to socialite Debbie Bancroft. She motioned toward her ample bosom, buttressed by a slinky floor-length, sequined gown.

“Unfortunately, we don’t have Dita von Teese this year, so Debbie’s the next best thing,” he said. (Last year, Ms. von Teese hung from a swing in the dinner tent.)

On the way out, the Transom spied a confused-looking horse, standing with handlers on the wooded pathway leading from the street. It sold to PR maven Vanessa Von Bismarck for $30,000.

The Transom soon found itself slightly tipsy and stranded in the Southampton Jitney station with a maxed-out credit card. We were about to stretch out on a bench for the night when we instead decided to climb into the SUV of a total stranger who walked in to drop off brochures for his high-end restaurant-delivery outfit, Dial-a-Dinner. His name was David Blum, and he professed himself a fan of good deeds. (This was when we texted his license plate to a friend).

Mr. Blum told us on the L.I.E. that the economy may be tanking, but rich people are still enjoying $35 pasta dishes in the privacy of their own homes. It’s less gaudy. (Or sometimes, they just don’t want people to know their sexual orientation or whom they’re dating). Business is up 37 percent since last year. In the Hamptons, he delivers from places like Nello and Nick & Toni’s. He’d just come from an event with Wolfgang Puck, who’s a friend.

He got his start at 18, as an undergrad at the University of Miami (he’s now 51). Delivering pizzas led to delivering steak and lobsters, which he now ferries over to people like Catherine Zeta-Jones and Michael Douglas. “Their birthday is on the same day,” he said. “So they have a few people over to their house—they live on Central Park West. They say, ‘Dial-a-Dinner, we want food from the Palm, we want steak and lobsters, we want delicious shrimp cocktail, we want a few bottles of wine, champagne, send it up.’” He even cleans up, aided by an army of employees in tuxedos.

“We get to see the homes of people like Diane Sawyer and Mike Nichols. We got to see Whoopi Goldberg’s, when she lived with Frank Langella.” Whoopi was not as tidy as Frank, Mr. Blum intimated. “Paul Simon lives in the same building as Lorne Michaels, in the same building as Alec Baldwin, on Central Park West. Paul Newman lives in the same building as Michael J. Fox. They’re all very nice people.

“We take care of Barry Diller,” he continued. “He likes Payard. He likes the Palm restaurant very much. Ron Perelman is a customer. Ron Perelman’s kosher at his house, very nice guy. Joel Klein…”

Mr. Blum is now taking his services to the air with a division called Jet Dining, which allows customers to eat fancy restaurant food on their private planes while flying to other fancy restaurants. “It’s becoming popular right now with some of the hedge fund people, who are extremely rich and want to try new experiences,” he said. He’ll send a private jet for them in Chicago, loaded up with food from the Palm, fly them to New York, put them up at the Pierre, send them to eat at Phillipe—“it’s very hard to get into”—and then fly them back to Chicago.

He’s looking to replicate this aboard helicopters. Everybody is into helicopter shares now. He has a meeting scheduled with Sikorsky, a chopper company. Was the Transom interested in a helicopter ride?

Mr. Blum can anticipate the movement of the financial markets based on who’s sending lobsters to whom, he said. He also once did the food for a party for Michael Jackson, before the singer decamped for Bahrain. “Very nice guy. Very soft spoken. You know who else was at that party? Ariel Sharon. It was very surreal.”